I have a close friend who I've know for 20 years. Over the last couple of years she's regularly asked me "can you lend me a fiver?" or "can you lend me a couple of quid?". Never big amounts, but little and regular. It's starting to grate on me that she never re-pays me. It's never for important stuff either...Just like if we're out and she wants to get an icecream or go for a coffee etc. She has a good job, lives with parents at home, no kids, no mortgage and no car. No debts that I'm aware of. Always goes on lavish holidays... Like shopping sprees to Dubai and heading to Japan next year.
I'm a bit of a pushover so I struggle to even consider asking for my money to be repaid, but just annoyed that she keeps asking for it.